Why the Best Bosses Are Flexible

I became a boss at UPS when I was only 21. I was a student at the University of Houston, working as a part-time supervisor for UPS at one of its many package-sorting hubs in that city. I still remember my manager instilling in me the importance of consistency. Be firm but fair, he said. Set expectations, create the ground rules – and then hold everybody to those standards equally.

There’s a lot of logic to that approach. But having managed people for more than 30 years now, I can also tell you that one of the most important traits any manager needs to develop is flexibility. You’re managing people, after all, and we all know that life can be unpredictable and messy. Manage long enough and you’ll find yourself dealing with a wide range of issues that aren’t covered neatly in your organization’s policy manual. My years have taught me that the best managers go with the flow, doing whatever it takes to support their people.

This isn’t just my opinion, either. A growing number of academic and workplace studies suggest that a flexible and adaptive leadership style generates higher productivity, worker satisfaction, and retention. For instance, a recent survey by WorkplaceTrends.com and CareerArc found that 75 percent of the employees polled ranked workplace flexibility as the most important benefit. Management consultant Roslyn Courtney argues that “ruthless flexibility” is also one of the key drivers of innovation.

I learned this lesson just months after I’d been assigned to manage other workers at a UPS package hub — many of whom, like myself, were working part-time to help pay for college. Handling and sorting packages has always been tough work, but maybe more so back then when there was less automation. You were expected to move at a brisk pace, safely, while assuring packages are where they’re supposed to be at any given second.

I remember one night during the busy holiday season, one of my employees – let’s call him Joe – came to me and said, “I’m sorry to do this to you now, Alan, but I’m going to have to quit.”

I knew Joe had been struggling to juggle college and the heavy number of hours he needed to work to pay for school. Between work, school and whatever else he had going on in his life, Joe was feeling the pressure. He also knew how much UPS counted on him and his fellow employees to work during the holiday season, and assumed that requesting time off for school during the holiday season wouldn’t make him popular.

But I saw a lot of potential in Joe and thought he was worth doing whatever it took to keep him. I figured if I gave him a few days off — even if I had to cover for him as well while ensuring that his co-workers didn’t get wind and all ask for time off too — Joe might come back refreshed and ready to go again. 

There was more than altruism at work. Sure, I cared about Joe as a person. But I also greatly valued Joe’s work and didn’t want to hire and train a new loader at what was our busiest time of the year. So I gave Joe five days off and told him to go focus on his exams. Joe accepted my offer and when he returned, he was ready to work.

I hadn’t thought about Joe in probably 30 years and a couple of months after I was promoted to the UPS Management Committee, I received a kind email one day from Joe.

Joe told me that after working that part-time job at UPS, he finished up college and earned his degree. Joe then joined the Army and rose to the rank of lieutenant. In that letter, Joe said his time at UPS – particularly when I gave him time off in a crunch – was a pivotal point in his life. And one of the lessons he learned at our company was the importance of putting the needs of others ahead of his own. That’s a lesson that served him well both in the military and in his personal relationships, he recalled.

Joe’s note was gracious, but in some ways I was simply following the lead of UPS’s founder, Jim Casey, who left a legacy of supporting his people. Many, many years ago, the company was negotiating a critical business deal, and during a particular late-night session Casey realized that he didn’t know enough about the legal intricacies to help from that point on.

Casey noticed that his lead negotiator was suffering from the flu, so he quietly slipped out a side door and trekked through the bitter cold to a pharmacy to buy a bottle of cough syrup for this employee.

That story always stuck with me – and helped me appreciate that sometimes the best way for managers to lead is by serving their people. Whether it’s producing a bottle of cough syrup or giving an employee the time off to tend to personal affairs, the best managers provide the right mix of motivation, accommodation and flexibility.

Alan Gershenhorn is Chief Commercial Officer at UPS.